Get a good web service like investor carrot and either hire someone to optimize it or learn it yourself lile I did. 

I mean negative money is not optimal

Aside from the management, there are many optimizations that are probably lacking which is why one property is drastically underperforming compared to another.

Does not make sense, I agree.Yes, extremely frustrating, but everyone's tax situation is different, and the only way to optimize your taxes is by working with a competent tax professional. 

Except for a few, select situations the whole concept of whole life insurance is sub-optimal.  

Sometimes solutions that under normal circumstances would be considered sub-optimal, or even crazy, may in fact be your best option. 

I don't see that, unless to argue that I could put financing on RE at less than 7% to optimize return. 

Vertical builds can optimize existing zoning.  

I'm a Software Engineer at a Big Tech and the numbers/optimization aspect of REI is what got me really interested in it.

Do everything you can to learn and minimize that risk, but remember you don't have an endless amount of time to figure this stuff out and conditions are never going to be optimal.